N&#39;-cyano-N-methyl-imidamide derivatives

ABSTRACT

The present invention relates to novel N′-cyano-N-methylimidamide derivatives of the general formula (I) 
     
       
         
         
             
             
         
       
         
         
           
             in which 
             n represents 2, 3, 4 or 5, 
             R represents optionally halogen-substituted C 1 -C 4 -alkyl, and 
             X represents halogen, where the substituents X may in each case be identical or different,
 
to processes for their preparation and to their use as pesticides.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP03/04808, filed May 8, 2003, whichwas published in German as International Patent Publication WO 03/095418on Nov. 20, 2003, which is entitled to the right of priority of GermanPatent Application 102 21 121.3, filed May 13, 2002.

The present invention relates to novel N′-cyano-N-methylimidamidederivatives, to a process for their preparation and to their use forcontrolling animal pests.

Certain N′-cyano-N-methylimidamide derivatives are already known (cf. WO91/04 965, WO 93/04032, EP 0 403 159 A2; DE 195 48 783 A1, J. Organomet.Chem. (1975), 97 (1), pp. 39-44; Bull. Soc. Chim. Belg. (1981), 90 (1),pp. 89-98 and in particular WO 00/03976). Insecticide properties of someof these compounds are also known (cf. EP 0 314 852 A1).

However, the activity of these compounds is not in every respectentirely satisfactory. Accordingly, it was an object of the presentinvention to provide further compounds having convincing activityagainst pests.

This invention now provides novel imidamide derivatives of the generalformula (I)

in which

-   n represents 2, 3, 4 or 5,-   R represents optionally halogen-substituted C₁-C₄-alkyl, and-   X represents halogen, where the different substituents X may in each    case be identical or different.

The N′-cyano-N-methylimidamide derivatives of the formula (I) can bepresent as optical and/or geometrical isomers. The present inventionrelates both to the different isomer mixtures and, in particular, to thepure isomers of the compounds according to the invention.

The novel N′-cyano-N-methylimidamide derivatives of the general formula(I) are obtained when amines of the formula (II)

in which

-   X and n are as defined above, are reacted-   (a) with N-cyanoalkylimidic acid esters of the formula (III)

-   -   in which    -   R is as defined above,    -   Q represents oxygen or sulfur and    -   Y represents alkyl,        in the presence of a diluent, or

-   (a′) with orthoesters of the formula (IV)

-   -   in which    -   R is as defined above, and    -   Y represents alkyl,        and cyanamide, if appropriate in the presence of a diluent, and

-   (b) subsequently alkylated by reacting the compounds, obtained    according to process (a) or (a′), of the formula (V)

-   -   in which    -   R, X and n are as defined above,    -   with compounds of the formula (VI)        CH₃-Z   (VI)    -   in which

-   Z represents a leaving group, for example halogen (for example    chlorine, bromine or iodine), mesylate or tosylate.

However, it is also possible to obtain the compounds of the formula (I)by reacting N-methylated amines of the formula (VII)

in which

-   X and n are as defined above,-   with N-cyanoalkylimidic acid esters of the formula (III) according    to process (a) or with orthoesters of the formula (IV) and Cyanamide    according to process (a′), the subsequent alkylation being    applicable.

The novel N′-cyano-N-methylimidamide derivatives of the general formula(I) have strongly pronounced biological properties and are suitableespecially for controlling animal pests, such as insects, arachnids, inparticular nematodes, encountered in agriculture, in forests, in theprotection of stored products and materials and also in the hygienesector.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents and ranges of the radicalslisted in the formulae given above and below are illustrated below.

-   n preferably represents 2, 3 or 4.-   R preferably represents optionally fluorine-, chlorine- or    bromine-substituted methyl, ethyl, n- or i-propyl or n-, i-, s- or    t-butyl.-   X preferably represents fluorine, chlorine or bromine.

If n represents 2, a first substituent X is preferably in theortho-position (2) and a second substituent X is preferably in thepara-position (4), or a first substituent X is preferably in themeta-position (3) and a second substituent X is preferably in thepara-position (4).

If n represents 3, a first substituent X is preferably in theortho-position (2), a second substituent X is in the para-position (4)and a third substituent X is in the meta-position (5) on the phenylring.

-   n particularly preferably represents 2 or 3.-   R particularly preferably represents optionally fluorine- or    chlorine-substituted methyl, ethyl or n- or i-propyl.-   X particularly preferably represents fluorine or chlorine.

If n represents 2, a first substituent X is particularly preferably inthe ortho-position (2) and a second substituent X is particularlypreferably in the para-position (4).

-   R very particularly preferably represents methyl or ethyl.

Particularly preferred compounds in the context of the above definitionsof substituents are compounds of the formulae (IA) to (IE):

Very particularly preferred compounds in the context of the abovedefinitions of substituents are compounds of the following formulae(IA¹) to (IE⁷):

The general or preferred radical definitions or illustrations givenabove apply to the end products and, correspondingly, to the startingmaterials and intermediates. These radical definitions can be combinedwith one another as desired, i.e. including combinations between therespective preferred ranges.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contains a combination of themeanings given above as being very particularly preferred.

In the radical definitions listed above and below, hydrocarbon radicals,such as alkyl, are in each case straight-chain or branched as far asthis is possible.

The amines of the general formula (II) and (VII) to be used as startingmaterial in the process according to the invention are generally knowncompounds of organic chemistry and/or can be obtained in a generallyknown manner, for example according to Houben-Weyl, Methoden derorganischen Chemie [Methods of organic chemistry], Volume XI, 1;Chantrapromma et al., J. Chem. Soc. Perkin Trans. 1 (1983), 1049-1062;Salerno et al., J. Org. Chem. 65 (2000), 3971-3981; Atkinson et al., J.Med. Chem. 26 (1983), 1353-1360; Kosugi et al., Bull. Chem. Soc. Jpn.,60 (1987), 767-68.

The formula (III) provides a general definition of theN-cyanoalkylimidic acid esters also required as starting materials forcarrying out the process (a) according to the invention. In thisformula, Y preferably represents C₁-C₄-alkyl, in particular methyl orethyl.

Most of the N-cyanoalkylimidic acid esters are known (cf., for example,U.S. Pat. No. 5,304,566 or J. Org. Chem. 28, 1963, 1816-1821) and/orthey can be obtained by customary processes.

The formula (IV) provides a general definition of the orthoesters alsorequired as starting materials for carrying out the process (a′)according to the invention. In this formula, Y preferably representsC₁-C₄-alkyl, in particular methyl or ethyl.

The compounds of the formula (IV) are compounds known to the personskilled in the art (cf. also Schäfer and Gewald, J. Prakt. Chem. 318,1976, 347-349).

The compounds of the formula (VI) used for the alkylation (methylation)of compounds of the formula (V) are likewise known compounds.

The process (a′) according to the invention can be carried out, forexample, analogously to Schäfer and Gewald, J. Prakt. Chem. 318, 1976,347-349, which describes the synthesis of arylaminoethylene cyanamides.

As described above, the processes (a) and (a′) according to theinvention can also be carried out using N-methylated amines of theformula (VII) as starting materials (see, for example, Edenhofer, Helv.Chim. Acta 58, 1975, 2192-2209); in this case, the subsequentmethylation is not applicable.

The processes according to the invention are preferably carried out inthe presence of a diluent which, in the case of process (a′), is notnecessarily required. Preference is given to using alcohols, such asmethanol and ethanol; nitrites, such as acetonitrile; or esters, such asethyl acetate. If appropriate, it may also be possible to carry out theprocesses according to the invention in water or organic-aqueousmixtures.

When carrying out the processes according to the invention, the reactionpartners are preferably employed in equimolar amounts; however, it isalso possible to use an excess of one or the other starting material.

When carrying out the processes according to the invention, the reactiontemperatures can be varied within a relatively wide range. In general,the processes are carried out at temperatures between 0° C. and 180° C.,preferably between 20° C. and 150° C., particularly preferably between20° C. and 80° C.

Work-up and isolation of the end products are carried out in a mannerknown to the person skilled in the art.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes, which are encountered inagriculture, in forestry, in the protection of stored products and ofmaterials, and in the hygiene sector, and have good plant tolerance andfavorable toxicity to warm-blooded animals. They may be preferablyemployed as plant protection agents. They are active against normallysensitive and resistant species and against all or some stages ofdevelopment. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare and Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus andScutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp. andSchistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae and Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp. andDamalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi and Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus and Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. and Psyllaspp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylustella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima and Tortrix viridana.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis and Costelytra zealandica.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis and Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp. and Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis andCeratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus andLatrodectus mactans.

From the order of Acarina, for example, Acarus siro, Argas spp.,Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptrutaoleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommaspp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp.,Tarsonemus spp., Bryobia praetiosa, Panonychus spp. and Tetranychus spp.

The phytoparasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursa phelenchus spp.

In particular, the compounds of the formula (I) according to theinvention have good nematicidal activity. Thus, they can be employedwith particularly good results for controlling Meloidogyne incognita.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and including the plant cultivars protectable or not protectableby plant breeders' rights. Plant parts are to be understood as meaningall parts and organs of plants above and below the ground, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds,roots, tubers and rhizomes. The plant parts also include harvestedmaterial, and vegetative and generative propagation material, forexample cuttings, tubers, rhizomes, offsets and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on their surroundings, environment or storage space bythe customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

The active compounds according to the invention can be converted intothe customary formulations, such as solutions, emulsions, wettablepowders, suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound and microencapsulations in polymericsubstances.

At appropriate application rates, some of the compounds according to theinvention have herbicidal activity.

These formulations are produced in a known manner, for example by mixingthe active compounds according to the invention with extenders, that isliquid solvents and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to employ for exampleorganic solvents as auxiliary solvents. Essentially, suitable liquidsolvents are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol and also their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulfoxide, and alsowater.

Suitable solid carriers are:

-   for example ammonium salts and ground natural minerals such as    kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or    diatomaceous earth, and ground synthetic minerals, such as highly    disperse silica, alumina and silicates; suitable solid carriers for    granules are: for example crushed and fractionated natural rocks    such as calcite, marble, pumice, sepiolite and dolomite, and also    synthetic granules of inorganic and organic meals, and granules of    organic material such as sawdust, coconut shells, corn cobs and    tobacco stalks; suitable emulsifiers and/or foam-formers are: for    example nonionic and anionic emulsifiers, such as polyoxyethylene    fatty acid esters, polyoxyethylene fatty alcohol ethers, for example    alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates,    arylsulfonates and also protein hydrolysates; suitable dispersants    are: for example lignosulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be present in itscustomary formulations and in the use forms, prepared from theseformulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides.Insecticides include, for example, phosphoric acid esters, carbamates,carboxylic esters, chlorinated hydrocarbons, phenyl ureas, compoundsprepared by microorganisms, inter alia.

Particularly advantageous co-components are, for example, the following:

Fungicides:

-   aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine,    azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl,    benzamacril, benzamacryl-isobutyl, bialaphos, binapacryl, biphenyl,    bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,    calcium polysulfide, capsimycin, captafol, captan, carbendazim,    carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,    chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,    cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,    debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezine,    dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,    diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione,    ditalimfos, dithianon, dodemorph, dodine, drazoxolon, edifenphos,    epoxiconazole, etaconazole, ethirimol, etridiazole, famoxadon,    fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,    fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin    hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,    fluquinconazole, flurprimidol, flusilazole, flusulfamide,    flutolanil, flutriafol, folpet, fosetyl-aluminum, fosetyl-sodium,    fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil,    furconazole, furconazole-cis, furmecyclox, guazatine,    hexachlorobenzene, hexaconazole, hymexazole, imazalil,    imibenconazole, iminoctadine, iminoctadine albesilate, iminoctadine    triacetate, iodocarb, ipconazole, iprobenfos (IBP), iprodione,    irumamycin, isoprothiolane, isovaledione, kasugamycin,    kresoxim-methyl, copper preparations, such as: copper hydroxide,    copper naphthenate, copper oxychloride, copper sulfate, copper    oxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb,    maneb, meferimzone, mepanipyrim, mepronil, metalaxyl, metconazole,    methasulfocarb, methfuroxam, metiram, metomeclam, metsulfovax,    mildiomycin, myclobutanil, myclozolin, nickel    dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace,    oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiin,    paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,    pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz,    procymidone, propamocarb, propanosine-sodium, propiconazole,    propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,    pyroxyfur, quinconazole, quintozene (PCNB), sulfur and sulfur    preparations, tebuconazole, tecloftalam, tecnazene, tetcyclacis,    tetraconazole, thiabendazole, thicyofen, thifluzamide,    thiophanate-methyl, thiram, tioxymid, tolclofos-methyl,    tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide,    trichlamide, tricyclazole, tridemorph, triflumizole, triforine,    triticonazole, uniconazole, validamycin A, vinclozolin,    viniconazole, zarilamide, zineb, ziram and also Dagger G, OK-8705,    OK-8801,    α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,    α-(2,4-dichlorophenyl)-β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,    α-(2,4-dichlorophenyl)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,    α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)phenyl]methylene]-1H-1,2,4-triazole-1-ethanol,    (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,    (E)-a-(methoxyimino)-N-methyl-2-phenoxyphenylacetamide, 1-isopropyl    {2-methyl-1-[[[1-(4-methylphenyl)ethyl]amino]carbonyl]propyl}carbamate,    1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone-O-(phenylmethyl)-oxime,    1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,    1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,    1-[(diiodomethyl)sulfonyl]-4-methyl-benzene,    1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]methyl]-1H-imidazole,    1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]methyl]-1H-1,2,4-triazole,    1-[1-[2-[(2,4-dichlorophenyl)methoxy]phenyl]ethenyl]-1H-imidazole,    1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,    2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,    2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methylcyclopropanecarboxamide,    2,6-dichloro-5-(methylthio)-4-pyrimidinylthiocyanate,    2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide,    2,6-dichloro-N-[[4-(trifluoromethyl)phenyl]methyl]benzamide,    2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,    2-[(1-methylethyl)sulfonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,    2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,    2-aminobutane, 2-bromo-2-(bromomethyl)pentanedinitrile,    2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,    2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)acetamide,    2-phenylphenol (OPP),    3,4-dichloro-1-[4-(difluoromethoxy)phenyl]-1H-pyrrole-2,5-dione,    3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)oxy]methyl]benzamide,    3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,    3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]pyridine,    4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide,    4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,    8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,    8-hydroxyquinoline sulfate,    9H-xanthene-2-[(phenylamino)carbonyl]-9-carboxylic hydrazide,    bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)oxy]-2,5-thiophenedicarboxylate,    cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,    cis-4-[3-[4-(1,1-dimethylpropyl)phenyl-2-methylpropyl]-2,6-dimethylmorpholine    hydrochloride, ethyl [(4-chlorophenyl)azo]cyanoacetate, potassium    bicarbonate, methanetetrathiolsodium salt, methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,    methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,    methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,    N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide,    N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)acetamide,    N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)acetamide,    N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulfonamide,    N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,    N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,    N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide,    N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,    N-[2,2,2-trichloro-1-[(chloroacetyl)amino]ethyl]-benzamide,    N-[3-chloro-4,5-bis(2-propinyloxy)phenyl]-N′-methoxy-methanimidamide,    N-formyl-N-hydroxy-DL-alaninesodium salt, O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]ethylphosphoramidothioate, O-methyl    S-phenyl phenylpropylphosphoramidothioate, S-methyl    1,2,3-benzothiadiazole-7-carbothioate,    spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran-3′-one.    Bactericides:-   Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulfate and other    copper preparations.    Insecticides/acaricides/nematicides:-   abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,    alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos    A, azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,    benfuracarb, bensultap, betacyfluthrin, bifenthrin, BPMC,    brofenprox, bromophos A, bufencarb, buprofezin, butocarboxim,    butylpyridaben, cadusafos, carbaryl, carbofuran, carbophenothion,    carbosulfan, cartap, CGA 157 419, CGA 184699, cloethocarb,    clorethoxyfos, chlordenvinphos, chlorfluazuron, chlormephos,    chlorpyrifos, chlorpyrifos M, cis-resmethrin, clocythrin,    clofentezin, cyanophos, cycloprothrin, cyflurthrin, cyhalotrin,    cyhexatin, cypermethrin, cyromazin, deltamethrin, demeton M, demeton    S, demeton-S-methyl, diafenthiuron, diazinon, dichlofenthion,    dichlorvos, dicliphos, dicrotophos, diethion, diflubenzuron,    dimethoate, dimethylvinphos, dioxathion, disulfoton, ediphenphos,    emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,    ethoprophos, etrimphos, fenamiphos, fenazaquin, fenbutatin oxide,    fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin,    fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam,    flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate,    fonophos, formothion, fosthiazate, fubfenprox, furathiocarb, HCH,    heptenophos, hexaflumuron, hexythiazox, imidacloprid, iprobenfos,    isazophos, isofenphos, isoprocarb, isoxathion, ivermectin,    lambda-cyhalothrin, lufenuron, malathion, mecarbam, mervinphos,    mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion,    methiocarb, methomyl, metolcarb, milbemectin, monocrotophos,    moxidectin, naled, NC 184, NI 25, nitenpyram, omethoate, oxamyl,    oxydemethon M, oxydeprofos, parathion A, parathion M, permethrin,    phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,    pirimicarb, pirimiphos M, pirimiphos A, profenofos, promecarb,    propaphos, propoxur, prothiofos, prothoate, pymetrozin,    pyrachlophos, pyradaphenthion, pyresmethrin, pyrethrum, pyridaben,    pyrimidifen, pyriproxifen, quinalphos, RH 5992, salithion, sebufos,    silafluofen, sulfotep, sulprofos, spinosad, tebufenozide,    tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, temephos,    terbam, terbufos, tetrachlorovinphos, thiafenox, thiodicarb,    thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin,    triarathen, triazophos, triazuron, trichlorfon, triflumuron,    trimethacarb, thiamethoxam, vamidothion, XMC, xylylcarb, YI    5301/5302, zetamethrin.

It is also possible to admix other known active compounds, such asherbicides, fertilizers and growth regulators.

When used as insecticides and nematicides, the active compoundsaccording to the invention can furthermore be present in theircommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with synergistic agents. Synergisticagents are compounds which increase the action of the active compounds,without it being necessary for the synergistic agent added to be activeitself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and pests of stored products, the activecompound is distinguished by an excellent residual action on wood andclay as well as a good stability to alkali on limed substrates.

At appropriate application rates, the compounds according to theinvention also have herbicidal properties and/or aplant-growth-regulating action, such as, for example, a defolianteffect.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattella germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropods which infest agriculturalproductive livestock, such as, for example, cattle, sheep, goats,horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys,ducks, geese and bees, other pets, such as, for example, dogs, cats,caged birds and aquarium fish, and also so-called test animals, such as,for example, hamsters, guinea pigs, rats and mice. By controlling thesearthropods, cases of death and reduction in productivity (for meat,milk, wool, hides, eggs, honey etc.) should be diminished, so that moreeconomic and easier animal husbandry is possible by use of the activecompounds according to the invention.

The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through process and suppositories, byparenteral administration, such as, for example, by injection(intramuscular, subcutaneous, intravenous, intraperitoneal and thelike), implants, by nasal administration, by dermal use in the form, forexample, of dipping or bathing, spraying, pouring on and spotting on,washing and powdering, and also with the aid of molded articlescontaining the active compound, such as collars, ear marks, tail marks,limb bands, halters, marking devices and the like.

When used for cattle, poultry, pets and the like, the active compoundsof the formula (I) can be used as formulations (for example powders,emulsions, free-flowing compositions), which comprise the activecompounds in an amount of from 1 to 80% by weight, directly or after 100to 10 000-fold dilution, or they can be used as a chemical bath.

It has furthermore been found that the compounds of the formula (I)according to the invention have a strong insecticidal action againstinsects which destroy industrial materials.

The following insects may be mentioned as examples and as preferred—butwithout a limitation:

Beetles, such as

-   Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,    Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,    Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus    africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,    Trogoxylon aequale, Minthes rugicollis, Xyleborus spec.,    Tryptodendron spec., Apate monachus, Bostrychus capucins,    Heterobostrychus brunneus, Sinoxylon spec., Dinoderus minutus.

Hymenopterons, such as

-   Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus    augur.

Termites, such as

-   Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,    Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes    lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,    Coptotermes formosanus.

Bristletails, such as Lepisma saccarina.

Industrial materials in the present connection are to be understood asmeaning non-living materials, such as, preferably, plastics, adhesives,sizes, papers and cards, leather, wood and processed wood products andcoating compositions.

Wood and processed wood products are materials to be protected,especially preferably, from insect infestation.

Wood and processed wood products which can be protected by the agentsaccording to the invention or mixtures comprising these are to beunderstood as meaning, for example: building timber, wooden beams,railway sleepers, bridge components, boat jetties, wooden vehicles,boxes, pallets, containers, telegraph poles, wood paneling, woodenwindow frames and doors, plywood, chipboard, joinery or wooden productswhich are used quite generally in house-building or in building joinery.

The active compounds can be used as such, in the form of concentrates orin generally customary formulations, such as powders, granules,solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersing agent and/or binder or fixing agent, awater repellent, if appropriate siccatives and UV stabilizers and ifappropriate dyestuffs and pigments, and also other processingauxiliaries.

The insecticidal compositions or concentrates used for the preservationof wood and wood-derived timber products comprise the active compoundaccording to the invention in a concentration of 0.0001 to 95% byweight, in particular 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thenature and occurrence of the insects and on the medium. The optimumamount employed can be determined for the use in each case by series oftests. In general, however, it is sufficient to employ 0.0001 to 20% byweight, preferably 0.001 to 10% by weight, of the active compound, basedon the material to be preserved.

Solvents and/or diluents which are used are an organic chemical solventor solvent mixture and/or an oily or oil-like organic chemical solventor solvent mixture of low volatility and/or a polar organic chemicalsolvent or solvent mixture and/or water, and if appropriate anemulsifier and/or wetting agent.

Organic chemical solvents which are preferably used are oily or oil-likesolvents having an evaporation number above 35 and a flashpoint above30° C., preferably above 45° C. Substances which are used as such oilyor oil-like water-insoluble solvents of low volatility are appropriatemineral oils or aromatic fractions thereof, or solvent mixturescontaining mineral oils, preferably white spirit, petroleum and/oralkylbenzene.

Mineral oils having a boiling range from 170 to 220° C., white spirithaving a boiling range from 170 to 220° C., spindle oil having a boilingrange from 250 to 350° C., petroleum and aromatics having a boilingrange from 160 to 280° C., terpentine oil and the like, areadvantageously employed.

In a preferred embodiment, liquid aliphatic hydrocarbons having aboiling range from 180 to 210° C. or high-boiling mixtures of aromaticand aliphatic hydrocarbons having a boiling range from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-like solvents of low volatility which have anevaporation number above 35 and a flashpoint above 30° C., preferablyabove 45° C., can be replaced in part by organic chemical solvents ofhigh or medium volatility, provided that the solvent mixture likewisehas an evaporation number above 35 and a flashpoint above 30° C.,preferably above 45° C., and that the insecticide/fungicide mixture issoluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, some of the organic chemicalsolvent or solvent mixture or an aliphatic polar organic chemicalsolvent or solvent mixture is replaced. Aliphatic organic chemicalsolvents containing hydroxyl and/or ester and/or ether groups, such as,for example, glycol ethers, esters or the like, are preferably used.

Organic chemical binders which are used in the context of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se, are water-dilutable and/or are soluble or dispersible oremulsifiable in the organic chemical solvents employed, in particularbinders consisting of or comprising an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenolic resin, hydrocarbon resin, such as indene-coumaroneresin, silicone resin, drying vegetable oils and/or drying oils and/orphysically drying binders based on a natural and/or synthetic resin.

The synthetic resin used as the binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances canalso be used as binders in an amount of up to 10% by weight. Dyestuffs,pigments, water-repelling agents, odor correctants and inhibitors oranticorrosive agents and the like which are known per se canadditionally be employed.

It is preferred according to the invention for the composition orconcentrate to comprise, as the organic chemical binder, at least onealkyd resin or modified alkyd resin and/or a drying vegetable oil. Alkydresins having an oil content of more than 45% by weight, preferably 50to 68% by weight, are preferably used according to the invention.

All or some of the binder mentioned can be replaced by a fixing agent(mixture) or a plasticizer (mixture). These additives are intended toprevent evaporation of the active compounds and crystallization orprecipitation. They preferably replace 0.01 to 30% of the binder (basedon 100% of the binder employed).

The plasticizers originate from the chemical classes of phthalic acidesters, such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoricacid esters, such as tributyl phosphate, adipic acid esters, such asdi-(2-ethylhexyl) adipate, stearates, such as butyl stearate or amylstearate, oleates, such as butyl oleate, glycerol ethers or highermolecular weight glycol ethers, glycerol esters and p-toluenesulfonicacid esters.

Fixing agents are based chemically on polyvinyl alkyl ethers, such as,for example, polyvinyl methyl ether or ketones, such as benzophenone orethylenebenzophenone.

Possible solvents or diluents are, in particular, also water, ifappropriate as a mixture with one or more of the abovementioned organicchemical solvents or diluents, emulsifiers and dispersing agents.

Particularly effective preservation of wood is achieved by impregnationprocesses on a large industrial scale, for example vacuum, double vacuumor pressure processes.

The ready-to-use compositions can also comprise other insecticides, ifappropriate, and also one or more fungicides, if appropriate.

Possible additional mixing partners are, preferably, the insecticidesand fungicides mentioned in Wo 94/29 268. The compounds mentioned inthis document are an explicit constituent of the present application.

Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, and triflumuron, and also fungicides, suchas epoxyconazole, hexaconazole, azaconazole, propiconazole,tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid,tolylfluanid, 3-iodo-2-propinylbutyl carbamate,N-octylisothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

As already metioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. By plant cultivars are meant plants having new properties(“traits”), bred either by conventional breeding, by mutagenesis or byrecombinant DNA techniques. They may be cultivars, biotypes andgenotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention, better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

The preferred transgenic plants or plant cultivars (i.e. those obtainedby genetic engineering) which are to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenseof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), corn, soybeans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapevines), and particular emphasis isgiven to corn, soybeans, potatoes, cotton and oilseed rape. Traits thatare emphasized are in particular increased defense of the plants againstinsects by toxins formed in the plants, in particular those formed bythe genetic material from Bacillus thuringiensis (for example by thegenes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c,Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelowreferred to as “Bt plants”). Traits that are also particularlyemphasized are increased defense of plants against fungi, bacteria andviruses by systematic acquired resistance (SAR), systemine,phytoalexins, elicitors and resistance genes and corresponding expressedproteins and toxins. Traits that are furthermore particularly emphasizedare the increased tolerance of the plants to certain herbicidally activecompounds, for example imidazolinones, sulfonylureas, glyphosate orphosphinotricin (for example the “PAT” gene). The genes which impart thedesired traits in question can also be present in combination with oneanother in the transgenic plants. Examples of “Bt plants” which may bementioned are corn varieties, cotton varieties, soybean varieties andpotato varieties which are sold under the trade names YIELD GARD® (forexample corn, cotton, soybeans), KnockOut® (for example corn), StarLink®(for example corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare corn varieties, cotton varieties and soybean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample corn, cotton, soybean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulfonylureas, for example corn).Herbicide-resistant plants (plants bred in a conventional manner forherbicide tolerance) which may be mentioned include the varieties soldunder the name Clearfield® (for example corn). Of course, thesestatements also apply to plant cultivars having these or still to bedeveloped genetic traits, which plants will be developed and/or marketedin the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or the mixturesspecifically mentioned in the present text.

The active compounds according to the invention act not only againstplant, hygiene and stored product pests, but also in the veterinarymedicine sector against animal parasites (ectoparasites), such as hardticks, soft ticks, mange mites, leaf mites, flies (biting and licking),parasitic fly larvae, lice, hair lice, feather lice and fleas. Theseparasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp. and Felicola spp.

From the order of the Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp. and Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp. and Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp. and Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattella germanica and Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Sternostoma spp. and Varroa spp.

From the order of the Actinedida (Prostigmata) und Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp. and Laminosioptes spp.

The preparation and the use of the active compounds according to theinvention is shown in the examples below.

PREPARATION EXAMPLES Example 1 (Process (a′))N′-Cyano-N-[1-(2,4-dichlorophenyl)ethyl]propaneimidamide (intermediateof formula (V))

1.85 g of 1-(2,4-dichlorophenyl)ethylamine, 1.63 g of trimethylorthopropionate and 0.46 g of Cyanamide were heated under reflux forabout 30 minutes. The volatile components were removed under reducedpressure and the residue was then titrated with water. Filtration anddrying gave 2.22 g ofN′-cyano-N-[1-(2,4-dichlorophenyl)ethyl]propaneimidamide of logP of2.56.

Example 2 (Process (b))N′-Cyano-N-[1-(2,4-dichlorophenyl)ethyl]-N-methylpropaneimidamide

1.00 g of N′-cyano-N-[1-(2,4-dichlorophenyl)ethyl]propaneimidamide wasdissolved in 25 ml of dimethylformamide, and 0.16 g of sodium hydride(60% pure in paraffin oil) was added at room temperature. After 30minutes, 0.63 g of iodomethane was added. The mixture was stirred atroom temperature overnight and, after removal of the solvent, purifiedchromatographically. This gave 0.86 g ofN′-cyano-N-[1-(2,4-dichlorophenyl)ethyl]-N-methylpropaneimidamide oflogP 2.80 and m.p. 148° C.

Analogously to examples 1 and 2 in accordance with the generaldescription of the preparation processes according to the invention, itis also possible to prepare, for example, the compounds of the generalformula (I) listed in table 1 below.

TABLE 1 (I)

Ex. No. Compound Physical data 3

m.p.: 101° C. 4

m.p.: 102° C. 5

m.p.: 104° C. 6

m.p.: 129° C. 7

logP: 2.40 8

logP: 2.61 9

m.p.: 125° C. 10

logP: 2.55 11

logP: 2.55 12

logP: 2.59 13

logP: 2.59 14

logP: 2.68 15

logP: 2.90 16

logP: 2.31 17

logP: 2.58 18

m.p.: 146-148° C. 19

logP: 2.90 20

logP: 3.18 21

logP: 2.94 22

logP: 2.19 23

logP: 2.40 24

logP: 2.46 25

logP: 2.94 26

logP: 2.09 27

logP: 2.32 28

logP: 2.37 29

logP: 2.59 30

logP: 2.66

The logP values given in table 1 were determined in accordance withEEC-Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18). Temperature: 43° C.

Mobile phases for the determination in the acidic range: 0.1% aqueousphosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (having 3 to16 carbon atoms) whose logP values are known (determination of the lopPvalues by the retention times using linear interpolation between twosuccessive alkanones).

USE EXAMPLES Example A Meloidogyne Test

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

After the desired period of time, the nematizidal activity is thedetermined in percent by the formation of galls. 100% means that nogalls were found; 0% means that the number of galls on the treatedplants corresponds to that of the untreated control.

In this test, for example, the following compounds of the PreparationExamples are highly effective: 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14,15, 17, 18, 19, 20, 22, 23, 24, 25, 26, 27, 28, 29.

Compared to the prior art, the compounds according to the invention are,in the test described above, at a given concentration of active compoundin ppm, clearly superior with respect to their efficacy (cf. Table II).The efficacy of the compounds is stated as kill rate in %.

Compounds according to the Compounds according to invention WO 00/03976

20 ppm: 100% 20 ppm: 0%

4 ppm: 100% 4 ppm: 0%

4 ppm: 100% 5 ppm: 0%

Example B Spodoptera frugiperda Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the Heerwurms (Spodoptera frugiperda)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed. 0% means that none of thecaterpillars have been killed.

In this test, Preparation Examples 5, 9 and 19 are highly effective.

Example C Phaedon Larvae Test

-   Solvent: 7 parts by weight of dimethylformamide-   Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed. 0% means that none of thebeetle larvae have been killed.

In this test, for example, the following compounds of the PreparationExamples are highly effective: 19.

1. A compound of formula (I)

in which n represents 2, 3, 4, or 5, R represents optionallyhalogen-substituted C₁-C₄-alkyl, and X represents halogen, where thedifferent substituents X may be identical or different.
 2. A process forpreparing a compound of formula (I) as claimed in claim 1 comprisingreacting a compound of formula (II)

in which X and n are as defined for formula (I) in claim 1, with (a) acompound of formula (III)

in which R is as defined for formula (I) in claim 1, Q represents oxygenor sulfur, and Y represents alkyl, or (a′) a compound of formula (IV)

in which R is as defined for formula (I) in claim 1, and Y representsalkyl, and cyanamide, optionally in the presence of a diluent, and (b)alkylating the compound obtained according to steps (a) or (a′) of theformula (V)

in which R, X, and n are as defined for formula (I) in claim 1, with acompound of formula (VI)CH₃-Z  (VI) in which Z represents a leaving group.
 3. A process forpreparing a compound of formula (I) as claimed in claim 1 comprisingreacting a compound of formula (VII)

in which X and n are as defined for formula (I) in claim 1, with (a) acompound of formula (III)

in which R is as defined for formula (I) in claim 1, Q represents oxygenor sulfur, and Y represents alkyl, or (a′) a compound of formula (IV)

in which R is as defined for formula (I) in claim 1, and Y representsalkyl, and cyanamide, optionally in the presence of a diluent.
 4. Acompound of formula (I) as claimed in claim 1 in which n represents 2,3, or 4, R represents optionally fluorine-, chlorine-, orbromine-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s-, ort-butyl, and X represents fluorine, chlorine, or bromine.
 5. A compoundof formula (I) as claimed in claim 1 in which n represents 2 or 3, Rrepresents optionally fluorine- or chlorine-substituted methyl, ethyl,or n- or i-propyl, and X represents fluorine or chlorine.
 6. A compoundof formula (I) as claimed in claim 1 in which R represents methyl orethyl.
 7. A pesticide comprising one or more compounds of formula (I) asclaimed in claim 1 and one or more extenders and/or surfactants.
 8. Amethod for controlling pests comprising allowing an effective amount ofa compound of formula (I) as claimed in claim 1 to act on pests and/ortheir habitat.
 9. A method for controlling pests comprising allowing aneffective amount of a composition as claimed in claim 7 to act on pestsand/or their habitat.
 10. A process for preparing pesticides comprisingmixing a compound of formula (I) as claimed in claim 1 with one or moreextenders and/or surfactants.